Pharmaceutical properties of 3-acyl-pyrrolidine-2,4-diones have been described (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). Furthermore, N-phenylpyrrolidine-2,4-diones have been synthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985 1095). A biological activity of these compounds has not been described.
EP-A-262 399 and GB-A-2 266 888 disclose compounds of a similar structure (3-aryl-pyrrolidine-2,4-diones); however, a herbicidal, insecticidal or acaricidal activity of these compounds is not known. Known to have herbicidal, insecticidal or acaricidal activity are unsubstituted bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-355 599 and EP-A-415 211) and substituted monocyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077).
Also known are polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-442 073) and 1H-arylpyrrolidine-dione derivatives (EP-A-456063, EP-A-521 334, EP-A-596 298, EP-A-613 884, EP-A-613 885, WO 94/01 997, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05 638, WO 98/06 721, WO 98/25 928, WO 99/16 748 and WO 99/24 437).
It is known that certain substituted A3-dihydrofuran-2-one derivatives have herbicidal properties (cf. DE-A-4 014 420). The synthesis of the tetronic acid derivatives used as starting materials (such as, for example, 3-(2-methyl-phenyl)-4-hydroxy-5-(4-fluorophenyl)-Δ3-dihydrofuran-2-one) has also been described in DE-A-4 014 420. Compounds of a similar structure are known from the publication Campbell et al., J. Chem. Soc., Perkin Trans. 1, 1985 (8) 1567-76, but an insecticidal and/or acaricidal activity has not been mentioned. Also known, from EP-A-528 156, EP-A-647 637, WO 95/26 345, WO 96/20 196, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05 638, WO 99/16 748 and WO 98/25 928, are 3-aryl-Δ3-dihydrofuranone derivatives having herbicidal, acaricidal and insecticidal properties. 3-Aryl-Δ3-dihydrothiophenone derivatives are also known (WO 95/26 345, WO 96/25 395, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05 638, WO 98/25 928, WO 99/16 748).
However, the herbicidal, acaricidal and insecticidal activity and/or the activity spectrum and the compatibility of these compounds with plants, in particular with respect to crop plants, is not always sufficient.